Production of polyazo coloring matters



. Patented Feb. 8, 1927.

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LAWRENCE HUGO FLETT, OF HAMBURG, BTEW YGRK, ASSIGNOR TO NATIONAL"'ANILINE 8; CHEMICAL CO, INCL, OF NEW YORK, N. Y., A COBIPORA'IION F NEWYORK.

No Drawing.

This invention relates to the production of new polyazo coloring matterswhich are of value for dyeing animal and other fibres or material. Thematerial dyed, stained or 5 printed with the new coloring matters alsoforms a part of the present invention.

The new coloring matters can be obtained by coupling three molecularproportions of the same or of different diazotized aromatic amino bodiesat least one of which contains an acid group, i. e., a carbonyl or asulfonic acid group, withone molecular proportion of resorcine which isfree from ,substi-tuents.

The new compounds correspond with the general formula wherein R, R and Brepresent aromatic hydrocarbon groups or radicals, more particularly ofthe benzene series, which may contain substituents, and in at leastone-of said aromatic radicals there is present an acid group, i. e., acarboxyl or a sulfonic acid group. 1

The new polyazo coloring matters in the dry and pulverizedstat-e and inthe shape of their alkali metal salts are soluble in water and ingeneral dye animal fibres and other material yellow to orange to brownshades. If desirable, they may becliromed.

The following specific example willfurther illustrate the invention, butit is understood that the invention is not limited thereto. The partsare by weight;

Example: 39 parts (2 mole) of the sodium salt of sulfanilic acid aredissolved in about 80 parts of water and diazotized in the usual mannerby the addition of about 33 parts of 50 B. sulfuric acid and 13.8 parts(2 mols) sodium nitrite, and the resulting diazo solution added to 11parts (1 mol) of resorcino dissolved in about parts of water, thetemperature being maintained at 0 10 C. After stirring about four hoursor more, about 10.6 parts of sodium carbonate are slowly added over aperiod of one-half ApplicationfiledA-pril 2, 1926. Serial No. 99,382. r

to one-hour and then' 22.7 parts of'a 47 B. caustic soda solution areadded, the solution being cooled to about 0 C. by any suitable means asby addition of ice. lTo'this solution there is then-added a diazotizedsolu, tion of 12.2 parts (1 mol) of commercial :gylidine (diazotized inthe usual manner at 0 C. by means of about 6.9 parts sodium nitrite and27 parts of 20 B. hydrochloric. acid) until a test with R-salt shows thepresence of a small excess of diazoxylidine. The alkaline reactionmixture is then neutralized by the a'dditionof hydrochloric acid andthedyestuff salted out by the addition of common salt, filtered off anddried. I

The new dyestuff thus obtained correspondsin the free state to theformula V p on i HoasN-=N wherein R represents a xylyl radical, and

NATO-scan in thedry state in the form of its sodium salt is a powdersoluble in water and dyes sumac or chrome mordanted leather excellentbrown shades.

wool. It stains wood chocolate shades.

It also dyes silk and In the above example, a purexylidine may i beemployed instead of a commercial xyli-' wherein R, R and R" representaromatic residues which may contain substituents, there being at leastone acid group present as a substituent in at least one of saidarowherein R, R and R represent aryl resimatic residues.

2. As new products, the polyazo coloring matterswhich correspond withthe formula dues of the benzene series which may contain substituents,there being present at least one acid group as a substituent in at leastone of said aryl residues.

3. As new products, the polyazo coloring matters which correspond withthe formula wherein R, R and R represent aryl resiiv dues which maycontain substituents, there being present atleast one sulfo group as asubstituent in at least one of said aryl resi-# dues. I V r 4. As newproducts, the polyazo coloring matters which correspond with the formulawherein R, R and R represent aryl residues which may containsubstituents, there being present at least one'acid group as asubstituent in'at least each of two of said aryl residues. 7

r .5. As'new products, the polyazo coloring matters which correspondwith the formula wherein R, R and R represent aryl radicals of thebenzene series which maycontain substituents, there being present atleast one sulfo group as a substituent in atleast each of two of thesaid aryl residues.

a 6. As new products, the polyazo coloring matters which in the freestate correspond with the formula wherein R, R and B represent arylhydrocarbon residues of the benzene series;

7. As a new product, the triazo coloring matter which in the free statecorresponds with the formula 13. Material dyed with coloringmatter ofclaim 6.

14. Material dyed with the coloring matter of claim 7.

In testimony whereof I aflix my signature.

LAVVRENGE HUGO FLETT.

